Asymmetric Total Syntheses of Naturally Occurring Indolosesquiterpene Alkaloids: Xiamycins and Oridamycins

Murmu, Ranjit (2024) Asymmetric Total Syntheses of Naturally Occurring Indolosesquiterpene Alkaloids: Xiamycins and Oridamycins. PhD thesis, Indian Institute of Science Education and Research Kolkata.

Text (PhD thesis of Ranjit Murmu (20RS064)) 20RS064.pdf - Submitted Version Restricted to Repository staff only Download (34MB)

Abstract

Indolosesquiterpene alkaloids are a growing class of architecturally complex secondary metabolites that were first isolated from a range of Streptomyces species in 2010. These alkaloids exhibit important biological activities such as antimicrobial, antiviral, antitumor, immunomodulatory, and enzyme inhibitory activities. In 2012, atropodiastereomeric indolosesquiterpenoid natural products, dixiamycins A and B were isolated independently by Zhang and Hertweck et al. and are having a rare N-N linkage leading to the axial chirality by sp³-hybridised N-N axis. Xiamycin A and its methyl ester are reported to display anti-HIV and antibiotic activities. Oridamycin A, the C-16 epimer, which exhibits modest activity against the water mold Saprolegnia parasitica having MIC value of 3.0 mg mL was isolated from Streptomyces sp. KS84 by Takada et al. As a part of my PhD thesis, I have undertaken the development of a catalytic asymmetric strategy for the total synthesis of these alkaloids to access them in significant quantities for further additional bio-profiles evaluation.

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